
Monthly Rentals in Wailea-Makena
Discover long-term rentals that feel like home for stays of a month or longer.
Nearby monthly rentals
Guest favorite

Condo in Wailea
4.93 out of 5 average rating, 167 reviewsStunning ocean view! 2/2 in the heart of Wailea
VinceRating, 5 stars2 months ago
I couldn't recommend Pat & Jim's condo enough. It was extremely clean and well-kept. Pat was extremely communicative and all instructions were super helpful and proactive. It felt like home immediately. The only downside, which is not unique to this condo, but I would guess applies to many condos in the Ekolu development, and probably other similar properties elsewhere in Wailea, is that it was a bit noisy. I'm an extremely light sleeper and, especially during the winter months at home, I am used to very quiet nights. Traffic and nature noises were significant for me at night, so I did have some difficulty sleeping. But this is just something to keep in mind if you're considering any condo in Wailea - as I said, it is not a unique feature of Pat & Jim's condo. If you're used to noise and/or are a heavy sleeper, this is absolutely, without question, the condo for you!
Guest favorite

Condo in Kihei
4.95 out of 5 average rating, 57 reviewsWailea Hidden Gem
JeanneRating, 5 stars1 week ago
We truly enjoyed our stay in Donna's unit. Besides being beautifully decorated and comfortable, the unit was immaculate, extremely well stocked in terms essentials such as kitchen items, bedding, beach accessories, bathroom accessories, and laundry. Parking was directly in front of the unit and the unit was an easy walk to the pool. We would not hesitate to book again in the future.
Guest favorite

Condo in Wailea
4.97 out of 5 average rating, 165 reviewsWailea Gem-Remodeled Ocean View
MargaretRating, 5 stars2 weeks ago
The location can't be beat and the condo grounds are stunning. The patio gets beautiful sunset views. Comfortable bed & having a 2nd bathroom is really nice.
Guest favorite

Condo in Kihei
4.93 out of 5 average rating, 122 reviewsNewly Remodeled 1bed/1bath, Kihei/Wailea
LisaRating, 5 stars3 months ago
Very nice place within walking distance to beaches and an easy quick drive to many restaurants
The comforts of home and great monthly rates
Amenities and perks for longer stays
Furnished rentals
Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.
Flexibility you need
Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*
Simple monthly prices
Special rates for long-term vacation rentals and a single monthly payment without additional charges.*
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*Some exclusions may apply in certain geographies and for some properties.